In March 2007 the presence of the light brown apple moth (LBAM), Epiphyas postvittana, was confirmed in California by the U.S. Department of Agriculture Animal and Plant Health Inspection Service (APHIS). It was first found in Alameda County and as of July 2007 has been found in eight San Francisco Bay area counties along with Monterey, Santa Cruz, and Los Angeles counties. APHIS issued a Federal Domestic Quarantine order on May 2, 2007, with restrictions on interstate shipment of plant material, and the California Department of Food and Agriculture (CDFA) issued a State Interior Quarantine order restricting intrastate shipment of plant material from counties where light brown apple moth is known to occur. The LBAM larvae cause damage to the leaves and fruit of apples, pears, grapes, citrus varieties, black and red currants, kiwifruit, hops, red and white clovers, lucerne, tree lupin, plantain, tutu, gorse, chrysanthemum, michaelmas daisy and other flowering plants, shrubs, especially acacias and conifers in the young stages of growth. The moth may have 2-4 generations annually in a temperate climate. Eggs are laid in clusters of 3 to 150 on leaves or fruit, which hatch to provide the larvae. To combat LBAM the pheromone 11E-tetradecen-1-yl acetate has been favorably employed.
The peach twig borer is one of the most significant pests on peach, nectarine, and apricot. The larvae of the overwintering generation emerge during bloom to petal fall and burrow into developing shoots. When populations are high these larvae can cause substantial damage to young trees. The first adults are usually detected during mid- to late May. Most economic damage results during the summer when larvae of summer generations attack the fruit. Insecticides are currently the most effective control tactic. Pre-bloom to petal fall sprays that target the young larvae provide the best control of the peach twig borer. Peach twig borer can damage stone fruits by feeding in shoots and causing shoot strikes, or by feeding directly on the fruit. Shoot damage is most severe on the vigorous growth of young, developing trees because feeding kills the terminal growth and can result in undesirable lateral branching. As fruit matures, it becomes highly susceptible to attack with damage most likely to occur from color break to harvest. Twig borer larvae generally enter fruit at the stem end or along the suture and usually feed just under the skin. To combat this insect the pheromone, 5E-decenyl acetate, has been employed.
The compound 8E 10,E-dodecadien-1-yl acetate has been found to be useful against destructive insects such as red pine shoot borer, hickory shuckworm, pea moth, chestnut tortrix, gorse pod moth, Chinese tortrix as well as other Lepidoptera. The corresponding alcohol, 8E, 10E-dodecadien-1-ol, has been found to be especially useful against the codling moth insect.
The black-headed budworm is the most significant defoliator of the coastal spruce-hemlock forests in the Western United States and Alaska. This insect is particularly common in southwest Alaska, the Prince William Sound area, and throughout southeast Alaska. The black-headed budworm's preferred host is western hemlock, but Sitka spruce and mountain hemlock are also frequently fed upon. The black-headed budworm (Acleris gloverana Walsingham) is a native insect of western North America. Until recently this insect was considered one species, Acleris variana (Fernald). Taxonomic studies show that various species are probably involved: three western species, A. gloverana, and an eastern species, A. variana. The range of A. gloverana is from northern California and areas in the Rocky Mountain northward into Yukon and Northwest Territories in Canada and southeastern Alaska. The eastern portion of the range of A. gloverana may overlap the western portion of the range of A. variana, which extends to the Atlantic seaboard. When conditions favor a high population of the black-headed budworm, the larvae cause extensive defoliation of hemlock spruce, and several species of fir trees of all ages may be killed, top-killed, or severely weakened. Widespread outbreaks, sometime covering millions of acres, have occurred periodically in the Pacific Northwest, British Columbia and coastal Alaska. The budworm has often been accompanied or followed by high populations of other defoliators such as the hemlock sawfly and the spruce budworm. An especially useful pheromone against blackheaded budworm is 11E,13-tetradecadienal.
The spruce budworm Choristoneura fumiferana (Clemens) is one of the most destructive native insects in the northern spruce and fir forests of the Eastern United States and Canada. Periodic outbreaks of the spruce budworm are a part of the natural cycle of events associated with the maturing of balsam fir. An especially effective pheromone against the spruce budworm is 11E-tetradecenal.
The compounds of this invention, including those pheromones mentioned above will generally have the formula (I)
wherein R2 is a branched or unbranched, saturated, ethylenically or mono or di unsaturated aliphatic radical, Z is —CH2OH, —CH2OAc or —CHO, m is a whole positive integer of one or more, generally from 1 to 20, and Ac is an acetyl group. The unsaturation can be any ethylenic unsaturation. While these compounds are effective pheromones to combat various insects many of the compounds of this formula are also useful as fragrances, such as for example, 5E-octenal.
While these synthetic pheromones and fragrances have been produced using synthesis procedures such as those disclosed in J. Amer. Chem. Soc., Vol. 112, pp 6615-6621 (1999) and U.S. Pat. No. 4,912,253 there is a need for a process to produce such compounds in greater yields. Also there is a need to be able to produce compounds of this type wherein the percentage of trans isomer is increased since the trans isomer of the pheromone compounds mentioned are generally more effective.